EP0311135A2 - Azoles et azines hétérocycliques substituées, procédé pour leur préparation et leur utilisation comme agents à activité herbicide - Google Patents

Azoles et azines hétérocycliques substituées, procédé pour leur préparation et leur utilisation comme agents à activité herbicide Download PDF

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Publication number
EP0311135A2
EP0311135A2 EP88116762A EP88116762A EP0311135A2 EP 0311135 A2 EP0311135 A2 EP 0311135A2 EP 88116762 A EP88116762 A EP 88116762A EP 88116762 A EP88116762 A EP 88116762A EP 0311135 A2 EP0311135 A2 EP 0311135A2
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Prior art keywords
general formula
group
halogen
radical
compound
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German (de)
English (en)
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EP0311135A3 (en
EP0311135B1 (fr
Inventor
Michael Dr. Ganzer
Wilfried Dr. Franke
Gabrielle Dr. Dorfmeister
Gerhard Dr. Johann
Friedrich Dr. Arndt
Richard Dr. Rees
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Bayer Pharma AG
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Schering AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C07D209/34—Oxygen atoms in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the invention relates to new heterocyclically substituted azoles and azines, processes for their preparation and their use as agents with herbicidal activity.
  • the object of the present invention is therefore to provide new compounds which do not have these disadvantages and are superior in their biological properties to the previously known compounds.
  • halogen stands for fluorine, chlorine, bromine or iodine.
  • haloalkyl means that one or more hydrogen atoms of the alkyl radical have been replaced by halogen.
  • heterocyclic rings are: pyrrole, oxazole, thiazole, imidazole, pyridine, oxazine, thiazine, pyrimidine, pyrazine, triazine, oxadiazine and thiadiazine and their di-, tetra- or optionally hexahydro derivatives.
  • the reaction according to process variant A) is expediently carried out at 20 ° C. to 200 ° C., if appropriate in a suitable solvent, 2,2-dimethylmaleic anhydride being used in a molar ratio of 1 to 3 equivalents to 1 equivalent of amine of the formula II.
  • the response time is 1 to 24 hours. It is convenient to carry out the reaction in the presence of an acid, such as acetic acid, for example by working in acetic acid as a solvent. However, it is also possible to react the two reactants using an inert solvent, such as, for example, dichloromethane or dimethyl sulfoxide, and the intermediate product Cyclize addition product with acid anhydrides, such as acetic anhydride.
  • anilines of the general formula II in which R 1 , X and Y have the meanings given under the general formula I, are by the usual process in aqueous, acidic suspension at a temperature of from -20 ° to + 10 ° C. with sodium nitrite diazotized, the reaction time being 0.5 to 3 hours.
  • the compounds of general formula XV can be cyclized with acid anhydrides, such as acetic anhydride, using a base, such as pyridine, in an inert solvent, such as ether, to give the compounds of formula I a.
  • acid anhydrides such as acetic anhydride
  • base such as pyridine
  • inert solvent such as ether
  • the reaction according to process variant C) is advantageously carried out at a temperature above 20 ° C., for example at 100 ° C. or at the reflux temperature of the reaction mixture.
  • the reactant is an anhydride of the general formula V
  • the reaction is advantageously carried out in the presence of an acid such as acetic acid, for example by working in acetic acid as a solvent.
  • an inert solvent such as dichloromethane or dimethyl sulfoxide
  • the reaction according to process variant D) takes place in an inert solvent at temperatures between 20 ° C. and 150 ° C., preferably at the boiling point of the solvent.
  • Suitable solvents are, for example, aliphatic and aromatic, optionally chlorinated hydrocarbons, such as petroleum ether, benzene, toluene, xylene, gasoline, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, and ethers, such as diethyl and di-n-butyl ether , Methyl tert-butyl ether, tetrahydrofuran, dioxane, ketones, such as, for example, acetone, methyl ethyl ketone, methyl isopropyl ketone, furthermore nitriles, such as acetonitrile and propionitrile, sulfoxides, such as dimethyl sulfoxide, or
  • the isocyanates or isothiocyanates of the general formula III used as starting material can be obtained from the anilines of the general formula II, in which R 1, X and Y have the meanings mentioned under the general formula I, by processes known per se with phosgene or thiophosgene or their easily produce reactive derivatives.
  • the reaction according to process variant E) takes place in an inert solvent, such as, for example, ether, methylene chloride, chloroform or ethyl acetate, at a temperature of from -50 ° C. to + 50 ° C. by reacting a compound of the general formula IIIa in which R 1, X and Y have the meanings mentioned under the general formula, with a compound of the general formula VIII in which R 12 , R 13 , R 14 , R 15 and T have the meanings mentioned under the general formula I.
  • the reaction time is 0.5 to 10 hours.
  • the compound of general formula XVI obtained is thermally unstable and is therefore preferably used in the next reaction without insulation.
  • Ring formation is carried out using an oxidizing agent in an organic solvent.
  • An inert solvent such as methylene chloride, chloroform, N, N-dimethylformamide and ethyl acetate can be used as the organic solvent.
  • the condensation reaction with ring formation can be carried out in the presence of effective acid acceptors, depending on the type of oxidizing agent.
  • Organic bases such as triethylamine, pyridine, dimethylaniline, inorganic bases, such as sodium hydroxide and sodium carbonate, are suitable as acid acceptors. Bromine, chlorine, sodium hypochlorite and others are used as oxidizing agents. If at least one substituent R stands for the hydroxyl group, iodine is preferred as the oxidizing agent.
  • the reaction according to process variant F) is advantageously carried out with catalysis in a suitable solvent.
  • the reaction temperatures are between room temperature and 150 C, preferably at the reflux temperature of the reaction mixture.
  • suitable solvents are: Wise called dimethyl sulfoxide, halogenated hydrocarbons such as methylene chloride and chloroform, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene, and other solvents inert to the reactants, such as diethyl ether, tetrahydrofuran or dimethylformamide.
  • Acids such as acetic acid or sulfuric acid, but also acidic ion exchangers can be used as catalysts.
  • the hydrazines of the general formula IV used as starting material in which R 1, X and Y have the meanings mentioned under the general formula I, are obtained by reacting compounds of the general formula II in acidic aqueous suspension at a temperature of from -20 ° C. to + 10 ° C with sodium nitrate and subsequent reaction with a reducing agent such as tin chloride.
  • the reaction according to process variants G) and H) can optionally be carried out with or without a solvent.
  • the reaction temperatures are between room temperature and 180 C, preferably at the reflux temperature of the reaction mixture.
  • Suitable solvents are methylene chloride, chloroform, benzene, toluene, chlorobenzene, dichlorobenzene or xylene, and other solvents which are inert to the reactants.
  • the reaction is preferably carried out in a solvent in a temperature range from 80 ° C to 200 ° C within 0.5 to 20 hours.
  • suitable solvents are toluene, xylene and acetic acid.
  • the reaction according to process variant I) is advantageously carried out with catalysis in a suitable solvent.
  • the reaction temperatures are between room temperature and 150 ° C, preferably at the reflux temperature of the reaction mixture.
  • suitable solvents are: Wise called dimethyl sulfoxide, halogenated hydrocarbons such as methylene chloride and chloroform, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene, and other solvents inert to the reactants, such as diethyl ether, tetrahydrofuran or dimethylformamide.
  • Acids such as acetic acid or sulfuric acid, but also acidic ion exchangers can be used as catalysts.
  • the reaction according to process variant J) takes place without or using a suitable inert solvent.
  • suitable solvents are dimethyl sulfoxide, halogenated hydrocarbons such as methylene chloride and chloroform, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene, and other solvents which are inert to the reactants, such as diethyl ether, tetrahydrofuran or dimethylformamide.
  • the starting compound of the general formula XII in which Ri, X, Y and R 9 have the meanings given under the general formula I, is obtained by using a hydrazine of the general formula IV, in which Ri, X and Y those under the general formula I have meanings, with an acid derivative of the formula XVIII, in which R 26 is a C 1 -C 4 -alkoxy radical or a halogen atom, reacted according to the following formula:
  • reaction according to process variant K) is advantageously carried out in a suitable solvent with the addition of a base, such as an alkali metal hydroxide or alcoholate, sodium hydride or triethylamine, optionally in a two-phase system with the addition of a phase transfer catalyst and at temperatures between 0 ° C. and 150 ° C. preferably carried out at the reflux temperature of the solvent.
  • a base such as an alkali metal hydroxide or alcoholate, sodium hydride or triethylamine
  • the reaction temperatures are between room temperature and 200 C, preferably at the boiling point of the solvent.
  • the starting materials are usually used in a stoichiometric ratio. However, an excess of one or the other can be advantageous in individual cases.
  • the compounds according to the invention prepared by the abovementioned processes can be isolated from the reaction mixture by the customary methods, for example by distilling off the solvent used under normal or reduced pressure or by extraction.
  • An increased degree of purity can generally be obtained by purification by column chromatography and by fractional distillation.
  • the compounds according to the invention are generally crystalline or viscous substances, some of which are readily soluble in halogenated hydrocarbons, such as chloroform, sulfoxides, such as dimethyl sulfoxide, or esters, such as ethyl acetate.
  • halogenated hydrocarbons such as chloroform
  • sulfoxides such as dimethyl sulfoxide
  • esters such as ethyl acetate
  • the active compounds according to the invention have a good herbicidal action on broad-leaved weeds and grasses.
  • a selective use of the active ingredients according to the invention is possible in different crops, for example in rapeseed, beets, soybeans, cotton, rice, barley, wheat and other types of cereals. Individual active ingredients are particularly suitable as selective herbicides in beets, cotton, soybeans and cereals.
  • the compounds for weed control in permanent crops for example forest, goatwood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and Hop plants, and for selective weed control in annual crops.
  • the application rates vary in the pre- or post-emergence between 0.05 and 5 kg / ha.
  • the compounds according to the invention can be used either alone, in a mixture with one another or with other active compounds. If necessary, other pesticides or pesticides can be added depending on the desired purpose. If it is intended to broaden the spectrum of activity, other herbicides can also be added. For example, those active ingredients which are listed in Weed Abstracts, Vol. 35, No.5, 1986, under the title "List of common names and abbreviations employed for currently used herbicides and plant growth regulators in Weed Abstracts" are suitable as herbicidally active mixture partners .
  • action-enhancing additives such as organic solvents, wetting agents and oils. Such additives may therefore allow the active ingredient dosage to be reduced.
  • Phospholipids can also be used as mixing partners, for example those from the group phosphatidylcholine, the hydrogenated phosphatidylcholines, phosphatidylethanolamine, the N-acylphosphatidylethanolamines, phosphatidylinositol, phosphatidylserine, lysolecithin and phosphatidylglycerol.
  • the labeled active ingredients or mixtures thereof are expedient in the form of preparations such as powders, scattering agents, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and, if appropriate, adhesives, wetting agents, emulsifiers and / or dispersing auxiliaries applied.
  • Suitable liquid carriers are, for example, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide, mineral oil fractions and vegetable oils.
  • Minerals for example bentonite, silica gel, talc, kaolin, attapulgite, limestone, and vegetable products, for example flours, are suitable as solid carriers.
  • Examples of surface-active substances include calcium ligninsulfonate, polyethylene alkylphenyl ether, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates and substituted benzenesulfonic acids and their salts.
  • the proportion of the active ingredient (s) in the various preparations can vary within wide limits.
  • the agents contain about 10 to 90 percent by weight of active ingredient, about 90 to 10 percent by weight of liquid or solid carriers and optionally up to 20 percent by weight of surface-active agents.
  • the agents can be applied in a customary manner, for example using water as a carrier in spray liquor amounts of about 100 to 1000 liters / ha.
  • Use of the agents in the so-called low-volume and ultra-low-volume process is just as possible as their application in the form of so-called microgranules.
  • preparations can be prepared in a manner known per se, for example by grinding or mixing processes. If desired, preparations of the individual components can also be mixed only shortly before they are used, as is done in practice, for example, in the so-called tank-mixing process.
  • Example 1.01 (Method E) 6- (6,6-Dimethyl-3,5,6,7-tetrahydropyrrolo [2,1-c] [1,2,4] thiadiazol-3-ylidenimino) -4- (2-propynyl) -2H-1 , 4-benzoxazin-3 (4H) -one
  • the listed plant species were treated with the listed compounds at a rate of 0.1 kg of active ingredient / ha after emergence.
  • the compounds were sprayed evenly over the plants as emulsions or suspensions with 500 liters of water / ha.
  • the compounds according to the invention showed a high crop selectivity with excellent activity against the weeds.
  • EHCG Echinochloa crus-galli
  • the listed plant species were treated with the listed compounds at a rate of 0.01 kg of active ingredient / ha after emergence.
  • the compounds were sprayed evenly over the plants as emulsions or suspensions with 500 liters of water / ha.
  • the compounds according to the invention showed a high crop selectivity with excellent activity against the weeds.
  • the comparative agent did not show the high effectiveness.
  • the plant species listed were treated with the listed compounds at a rate of 0.1 kg of active ingredient / ha before emergence.
  • the compounds were sprayed evenly over the plants as emulsions or suspensions with 500 liters of water / ha.
  • the compounds according to the invention showed a high crop selectivity in sugar beet, wheat and maize with excellent activity against the weeds.
  • the comparative agent did not show the same selectivity.
  • the listed plant species were treated with the listed compounds at a rate of 0.1 kg of active ingredient / ha after emergence.
  • the compounds were sprayed evenly over the plants as emulsions or suspensions with 500 liters of water / ha.
  • the compounds according to the invention showed a high crop selectivity in maize with excellent activity against the weeds.
  • the comparative agent did not show the same selectivity.
  • the plant species listed were treated with the listed compounds at a rate of 0.1 kg of active ingredient / ha before emergence.
  • the compounds were sprayed evenly over the plants as emulsions or suspensions with 500 liters of water / ha.
  • the compounds according to the invention showed an excellent action against the weeds.
  • the listed plant species were treated with the listed compounds at a rate of 0.1 kg of active ingredient / ha after emergence.
  • the compounds were sprayed evenly over the plants as emulsions or suspensions with 500 liters of water / ha.
  • the compounds according to the invention showed a high crop selectivity in wheat with excellent activity against the weeds.
  • the listed plant species were treated with the listed compounds at a rate of 0.3 kg of active ingredient / ha after emergence.
  • the compounds were sprayed evenly over the plants as emulsions or suspensions with 500 liters of water / ha.
  • the compounds according to the invention showed a high crop selectivity in wheat and corn with excellent activity against the weeds.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
EP88116762A 1987-10-09 1988-10-10 Azoles et azines hétérocycliques substituées, procédé pour leur préparation et leur utilisation comme agents à activité herbicide Expired - Lifetime EP0311135B1 (fr)

Priority Applications (1)

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AT88116762T ATE90091T1 (de) 1987-10-09 1988-10-10 Heterocyclisch substituierte azole und azine, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung.

Applications Claiming Priority (2)

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DE19873734745 DE3734745A1 (de) 1987-10-09 1987-10-09 Tetrahydropyrrolo(2,1-c)(1,2,4)-thiadiazol-3-ylideniminobenzoxazinone und andere heterocyclisch substituierte azole und azine, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung
DE3734745 1987-10-09

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EP0311135A2 true EP0311135A2 (fr) 1989-04-12
EP0311135A3 EP0311135A3 (en) 1989-09-06
EP0311135B1 EP0311135B1 (fr) 1993-06-02

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EP (1) EP0311135B1 (fr)
JP (1) JP2765873B2 (fr)
KR (1) KR890006615A (fr)
CN (1) CN1032479A (fr)
AR (1) AR244235A1 (fr)
AT (1) ATE90091T1 (fr)
AU (1) AU614775B2 (fr)
BR (1) BR8805182A (fr)
DD (1) DD282847A5 (fr)
DE (2) DE3734745A1 (fr)
DK (1) DK563488A (fr)
ES (1) ES2058206T3 (fr)
FI (1) FI92585C (fr)
HU (1) HU207330B (fr)
IL (1) IL87887A (fr)
PH (1) PH27146A (fr)
SU (1) SU1722204A3 (fr)
ZA (1) ZA887559B (fr)

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EP0351676A2 (fr) * 1988-07-21 1990-01-24 Nihon Bayer Agrochem K.K. Benzothiazolones
US4902335A (en) * 1987-06-22 1990-02-20 Nihon Tokushu Noyaku Seizo K.K. Benzo-fused cyclic compounds
WO1990015057A1 (fr) * 1989-06-09 1990-12-13 Ciba-Geigy Ag Composes heterocycliques
EP0406993A2 (fr) * 1989-07-07 1991-01-09 Schering Aktiengesellschaft Dérivés de benzoxazolinone et benzoxazinone substituées, leur procédé de préparation et leur utilisation comme agent à activité herbicide
EP0420194A2 (fr) * 1989-09-26 1991-04-03 Sumitomo Chemical Company, Limited Dérivés d'uraciles, leur préparation et leur utilisation
EP0427484A1 (fr) * 1989-11-09 1991-05-15 Rohm And Haas Company Nouveaux composés benzoxazoloniques et leur utilisation à titre de microbicides
EP0408382A3 (en) * 1989-07-14 1991-07-10 Nissan Chemical Industries, Limited Uracil derivatives and herbicides containing the same as active ingredient
EP0444764A1 (fr) * 1990-02-27 1991-09-04 Schering Aktiengesellschaft Procédé et intermédiaires de préparation de 1-benzothiazolyl-3,4-diméthyl-3-pyrroline-2,5-diones substituées
DE4008691A1 (de) * 1990-03-15 1991-09-19 Schering Ag Verfahren und zwischenprodukte zur herstellung von substituierten 6-(3,5,6,7-tetrahydropyrrolo(2,1-c)(1,2,4)-thiadiazol-3-ylidenimino)-7-fluor-2h-1,4-benzoxazin-3(4h)-onen
EP0448188A2 (fr) * 1990-03-15 1991-09-25 Schering Aktiengesellschaft Procédé et composés intermédiaires pour la préparation de 6-(3,5,6,7-tétrahydropyrrolo-[2,1-c][1,2,4]-thiazol-3-ylidène-imino)-7-fluoro-2H-1,4-benzoxazin-3(4H)-ones substituées
EP0456334A2 (fr) * 1990-04-12 1991-11-13 Schering Aktiengesellschaft Composition herbicide à activité synergique
US5084084A (en) * 1989-07-14 1992-01-28 Nissan Chemical Industries Ltd. Uracil derivatives and herbicides containing the same as active ingredient
US5156668A (en) * 1989-10-12 1992-10-20 Sumitomo Chemical Company, Limited Benzoxazinyl-pyrazoles and their use as herbicides
WO1992020675A1 (fr) * 1991-05-24 1992-11-26 Schering Aktiengesellschaft Derives de benzothiazole substitues, leur preparation et utilisation comme herbicides
DE4125246C1 (fr) * 1991-07-26 1993-02-04 Schering Ag Berlin Und Bergkamen, 1000 Berlin, De
WO1993005655A1 (fr) * 1991-09-23 1993-04-01 Schering Aktiengesellschaft Compositions herbicides synergiques
WO1993008689A1 (fr) * 1991-11-05 1993-05-13 Schering Aktiengesellschaft Compositions herbicides a activite synergique
EP0549892A1 (fr) * 1991-12-31 1993-07-07 American Cyanamid Company Indolinones substitués utilisables comme agents herbicides
US5238906A (en) * 1990-11-27 1993-08-24 Sumitomo Chemical Company, Limited Pyridone derivatives and use
WO1993019065A1 (fr) * 1992-03-17 1993-09-30 Schering Aktiengesellschaft Procede et intermediaires destines a la preparation de d,l-2-(7-fluoro-3,4-dihydro-3-oxo-2h-1,4-benzoxazin-6-yl)-perhydroimidazo[1,5-a]pyridine-1,3-diones substitues
EP0572852A1 (fr) * 1992-05-30 1993-12-08 BASF Aktiengesellschaft Quinoxalines-2,3(1H,4H)-diones utiles comme médicament
US5314864A (en) * 1989-09-26 1994-05-24 Sumitomo Chemical Company, Limited N-aminouracil derivatives, and their production and use
US5322835A (en) * 1988-04-20 1994-06-21 Sumitomo Chemical Company, Limited N-phenylimides, and their production and use
WO1994018837A1 (fr) * 1993-02-20 1994-09-01 Schering Aktiengesellschaft Compositions herbicides
WO1994018836A1 (fr) * 1993-02-17 1994-09-01 Schering Aktiengesellschaft Composition herbicide synergique a base de thidiazimine
US5354730A (en) * 1989-10-02 1994-10-11 Sumitomo Chemical Company, Limited Uracil derivatives and their herbicidal use
ES2072804A1 (es) * 1992-10-08 1995-07-16 Schering Ag Derivados de benzotiazoles sustituidos, procedimiento para producirlos y composiciones herbicidas que los contienen.
US5494889A (en) * 1991-06-06 1996-02-27 Ciba-Geigy Corporation Herbicides
US5728651A (en) * 1993-03-26 1998-03-17 E. I. Du Pont De Nemours And Company Herbicidal triazolinones
US6306851B1 (en) 1999-05-04 2001-10-23 American Home Products Corporation Cyclocarbamate and cyclic amide derivatives
US6319912B1 (en) 1999-05-04 2001-11-20 American Home Products Corporation Cyclic regimens using 2,1-benzisothiazoline 2,2-dioxides
WO2001090102A2 (fr) * 2000-05-24 2001-11-29 Bayer Aktiengesellschaft 6-heteroclyclyl-3-oxo-3,4-dihydro-quinoxalines
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US6355648B1 (en) 1999-05-04 2002-03-12 American Home Products Corporation Thio-oxindole derivatives
US6358947B1 (en) 1999-05-04 2002-03-19 American Home Products Corporation Tetracyclic progesterone receptor modulator compounds and methods
US6358948B1 (en) 1999-05-04 2002-03-19 American Home Products Corporation Quinazolinone and benzoxazine derivatives as progesterone receptor modulators
US6369056B1 (en) 1999-05-04 2002-04-09 American Home Products Corporation Cyclic urea and cyclic amide derivatives
US6380178B1 (en) 1999-05-04 2002-04-30 American Home Products Corporation Cyclic regimens using cyclocarbamate and cyclic amide derivatives
US6380235B1 (en) 1999-05-04 2002-04-30 American Home Products Corporation Benzimidazolones and analogues
WO2002038562A1 (fr) * 2000-11-08 2002-05-16 Sumitomo Chemical Takeda Agro Company, Limited Derives de triazolone bicycliques et herbicides contenant ces derniers
US6391907B1 (en) 1999-05-04 2002-05-21 American Home Products Corporation Indoline derivatives
US6399593B1 (en) 1999-05-04 2002-06-04 Wyeth Cyclic regimens using cyclic urea and cyclic amide derivatives
US6407101B1 (en) 1999-05-04 2002-06-18 American Home Products Corporation Cyanopyrroles
US6417214B1 (en) 1999-05-04 2002-07-09 Wyeth 3,3-substituted indoline derivatives
US6423699B1 (en) 1999-05-04 2002-07-23 American Home Products Corporation Combination therapies using benzimidazolones
US6436929B1 (en) 1999-05-04 2002-08-20 Wyeth Cyclothiocarbamate derivatives as progesterone receptor modulators
US6444668B1 (en) 1999-05-04 2002-09-03 Wyeth Combination regimens using progesterone receptor modulators
US6462032B1 (en) 1999-05-04 2002-10-08 Wyeth Cyclic regimens utilizing indoline derivatives
US6498154B1 (en) 1999-05-04 2002-12-24 Wyeth Cyclic regimens using quinazolinone and benzoxazine derivatives
US6509334B1 (en) 1999-05-04 2003-01-21 American Home Products Corporation Cyclocarbamate derivatives as progesterone receptor modulators
WO2012041789A1 (fr) 2010-10-01 2012-04-05 Basf Se Benzoxazinones herbicides
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EP4091450A1 (fr) * 2021-05-19 2022-11-23 Syngenta Crop Protection AG Dérivés de 3,3-difluoro-2-oxoindoline utiles dans un procédé de désherbage

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US4902335A (en) * 1987-06-22 1990-02-20 Nihon Tokushu Noyaku Seizo K.K. Benzo-fused cyclic compounds
US5322835A (en) * 1988-04-20 1994-06-21 Sumitomo Chemical Company, Limited N-phenylimides, and their production and use
EP0351676A2 (fr) * 1988-07-21 1990-01-24 Nihon Bayer Agrochem K.K. Benzothiazolones
EP0351676A3 (fr) * 1988-07-21 1990-06-27 Nihon Bayer Agrochem K.K. Benzothiazolones
WO1990015057A1 (fr) * 1989-06-09 1990-12-13 Ciba-Geigy Ag Composes heterocycliques
EP0406993A2 (fr) * 1989-07-07 1991-01-09 Schering Aktiengesellschaft Dérivés de benzoxazolinone et benzoxazinone substituées, leur procédé de préparation et leur utilisation comme agent à activité herbicide
EP0406993A3 (en) * 1989-07-07 1991-12-27 Schering Aktiengesellschaft Berlin Und Bergkamen Substituted benzoxazolinone and benzoxazinone derivatives, process for their preparation and their use as agent with herbicide activity
EP0408382A3 (en) * 1989-07-14 1991-07-10 Nissan Chemical Industries, Limited Uracil derivatives and herbicides containing the same as active ingredient
US5084084A (en) * 1989-07-14 1992-01-28 Nissan Chemical Industries Ltd. Uracil derivatives and herbicides containing the same as active ingredient
US5127935A (en) * 1989-07-14 1992-07-07 Nissan Chemical Industries Ltd. Uracil derivatives and herbicides containing the same as active ingredient
US5154755A (en) * 1989-07-14 1992-10-13 Nissan Chemical Industries Ltd. Uracil derivatives and herbicides containing the same as active ingredient
EP0420194A2 (fr) * 1989-09-26 1991-04-03 Sumitomo Chemical Company, Limited Dérivés d'uraciles, leur préparation et leur utilisation
EP0420194A3 (en) * 1989-09-26 1991-06-12 Sumitomo Chemical Company, Limited Uracil derivatives and their production and use
US5314864A (en) * 1989-09-26 1994-05-24 Sumitomo Chemical Company, Limited N-aminouracil derivatives, and their production and use
US5354730A (en) * 1989-10-02 1994-10-11 Sumitomo Chemical Company, Limited Uracil derivatives and their herbicidal use
US5156668A (en) * 1989-10-12 1992-10-20 Sumitomo Chemical Company, Limited Benzoxazinyl-pyrazoles and their use as herbicides
EP0427484A1 (fr) * 1989-11-09 1991-05-15 Rohm And Haas Company Nouveaux composés benzoxazoloniques et leur utilisation à titre de microbicides
EP0444764A1 (fr) * 1990-02-27 1991-09-04 Schering Aktiengesellschaft Procédé et intermédiaires de préparation de 1-benzothiazolyl-3,4-diméthyl-3-pyrroline-2,5-diones substituées
EP0448188A3 (en) * 1990-03-15 1992-02-26 Schering Aktiengesellschaft Process and intermediates for the preparation of substituted 6-(3,5,6,7-tetrahydropyrrolo-(2,1-c)(1,2,4)-thiadiazol-3-ylidenimino)-7-fluoro-2h-1,4-benzoxazin-3(4h)-ones
DE4008691A1 (de) * 1990-03-15 1991-09-19 Schering Ag Verfahren und zwischenprodukte zur herstellung von substituierten 6-(3,5,6,7-tetrahydropyrrolo(2,1-c)(1,2,4)-thiadiazol-3-ylidenimino)-7-fluor-2h-1,4-benzoxazin-3(4h)-onen
EP0448188A2 (fr) * 1990-03-15 1991-09-25 Schering Aktiengesellschaft Procédé et composés intermédiaires pour la préparation de 6-(3,5,6,7-tétrahydropyrrolo-[2,1-c][1,2,4]-thiazol-3-ylidène-imino)-7-fluoro-2H-1,4-benzoxazin-3(4H)-ones substituées
EP0456334A2 (fr) * 1990-04-12 1991-11-13 Schering Aktiengesellschaft Composition herbicide à activité synergique
EP0456334A3 (en) * 1990-04-12 1992-04-22 Schering Aktiengesellschaft Heribicidal composition with synergistic activity
US5238906A (en) * 1990-11-27 1993-08-24 Sumitomo Chemical Company, Limited Pyridone derivatives and use
US5424443A (en) * 1991-05-24 1995-06-13 Schering Aktiengesellschaft Substituted benzothiazole derivatives, their preparation and use as herbicides
WO1992020675A1 (fr) * 1991-05-24 1992-11-26 Schering Aktiengesellschaft Derives de benzothiazole substitues, leur preparation et utilisation comme herbicides
US5494889A (en) * 1991-06-06 1996-02-27 Ciba-Geigy Corporation Herbicides
WO1993003043A1 (fr) * 1991-07-26 1993-02-18 Schering Aktiengesellschaft PROCEDE ET PRODUITS INTERMEDIAIRES POUR LA FABRICATION DE 6-(3,5,6,7-TETRAHYDROPYROLLO[2,1-c][1,2,4]THIADIAZOL-3-YLIDENAMINO)-7-FLUOR-2H-1,4-BENZOXAZIN-3(4H)-ONES SUBSTITUES
DE4125246C1 (fr) * 1991-07-26 1993-02-04 Schering Ag Berlin Und Bergkamen, 1000 Berlin, De
WO1993005655A1 (fr) * 1991-09-23 1993-04-01 Schering Aktiengesellschaft Compositions herbicides synergiques
TR26286A (tr) * 1991-09-23 1995-02-15 Schering Ag 6-(6,6-dimetil-3,5,6,7-tetrahidropirrolo-(2,1-c) (1,2,4)tiadiazol-3-ilidenimo)-7-floro-4-(2-propi- nil)-2h-1,4-benzoksazin-3(4h)-on ile baska bir sinerjist özellikte herbisid terkipleri.
WO1993008689A1 (fr) * 1991-11-05 1993-05-13 Schering Aktiengesellschaft Compositions herbicides a activite synergique
EP0549892A1 (fr) * 1991-12-31 1993-07-07 American Cyanamid Company Indolinones substitués utilisables comme agents herbicides
WO1993019065A1 (fr) * 1992-03-17 1993-09-30 Schering Aktiengesellschaft Procede et intermediaires destines a la preparation de d,l-2-(7-fluoro-3,4-dihydro-3-oxo-2h-1,4-benzoxazin-6-yl)-perhydroimidazo[1,5-a]pyridine-1,3-diones substitues
EP0572852A1 (fr) * 1992-05-30 1993-12-08 BASF Aktiengesellschaft Quinoxalines-2,3(1H,4H)-diones utiles comme médicament
AU660799B2 (en) * 1992-05-30 1995-07-06 Basf Aktiengesellschaft 2,3 (1H,4H)-quinoxalinediones
US5714489A (en) * 1992-05-30 1998-02-03 Basf Aktiengesellschaft 2,3(1H,4H)quinoxalinedione
ES2072804A1 (es) * 1992-10-08 1995-07-16 Schering Ag Derivados de benzotiazoles sustituidos, procedimiento para producirlos y composiciones herbicidas que los contienen.
WO1994018836A1 (fr) * 1993-02-17 1994-09-01 Schering Aktiengesellschaft Composition herbicide synergique a base de thidiazimine
WO1994018837A1 (fr) * 1993-02-20 1994-09-01 Schering Aktiengesellschaft Compositions herbicides
US5728651A (en) * 1993-03-26 1998-03-17 E. I. Du Pont De Nemours And Company Herbicidal triazolinones
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EP3278667A1 (fr) 2016-08-05 2018-02-07 Basf Se Méthode de contrôle de mauvaises herbes résistantes aux inhibiteurs de la ppo
WO2019101551A1 (fr) 2017-11-23 2019-05-31 Basf Se Phényléthers herbicides
WO2019101513A1 (fr) 2017-11-23 2019-05-31 Basf Se Pyridyléthers en tant qu'herbicides
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ATE90091T1 (de) 1993-06-15
DD282847A5 (de) 1990-09-26
JP2765873B2 (ja) 1998-06-18
DK563488D0 (da) 1988-10-07
AR244235A1 (es) 1993-10-29
DK563488A (da) 1989-04-10
FI92585C (fi) 1994-12-12
ZA887559B (en) 1989-06-28
FI884625A0 (fi) 1988-10-07
EP0311135A3 (en) 1989-09-06
BR8805182A (pt) 1989-05-23
IL87887A0 (en) 1989-03-31
HUT49356A (en) 1989-09-28
AU2356888A (en) 1989-04-13
HU207330B (en) 1993-03-29
CN1032479A (zh) 1989-04-26
SU1722204A3 (ru) 1992-03-23
KR890006615A (ko) 1989-06-14
JPH01157977A (ja) 1989-06-21
DE3881468D1 (de) 1993-07-08
ES2058206T3 (es) 1994-11-01
DE3734745A1 (de) 1989-04-20
EP0311135B1 (fr) 1993-06-02
PH27146A (en) 1993-04-02
FI884625A (fi) 1989-04-10
IL87887A (en) 1993-04-04
FI92585B (fi) 1994-08-31
AU614775B2 (en) 1991-09-12

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